34915-82-7Relevant academic research and scientific papers
ORGANIC DISULFIDES AND RELATED SUBSTANCES. 48. CYCLIC DI- AND TRISULFIDES BASED ON 1,4-DITHIOLS
Singh, Pramod K.,Field, Lamar,Sweetman, Brian J.
, p. 61 - 72 (2007/10/02)
Based on 1,4-dithiols, the seven-membered cyclic trisulfide 1,5-dihydro-2,3,4-benzotrithiepin (3), the nonbenzenoid counterpart (17), related oxides, and open-chain analogs were investigated.The monoxide 4a, n = 1, of 3 upon oxidation lost sulfur and gave 1,4-dihydro-2,3-benzodithiin-2-monoxide (12a, n = 1).The 2,2-dioxide (4b, n = 2) could not be isolated; only 4a, 12a, or 1,4-dihydro-2,3-benzodithiin-2,2-dioxide (12b, n = 2) could be obtained.With related open-chain disulfides in the benzo series of the structure 1,2-(RSSCH2)2C6H4, when R was -(CH2)4SO2Na, ca. 50percent disproportionation occured in H2O in ca. 0.5 h, but the unsymmetrical disulfides with R = p-CH3C6H4- or HOCH2CH(OH)CH2- were relatively stable.The nonbenzenoid counterpart of 3, i.e. 4,7-dihydro-1,2,3-trithiepin (17) could not be obtained pure from the appropriate dichloride (19a), Bunte salt 16a or thiosulfonate (22a), nor could be the disulfide counterpart of 17, i.e. 3,6-dihydro-1,2-dithiin (23), be oxidized to the 1,1-dioxide 24.Bisdisulfides (14ab; 15ab), however, could be obtained satisfactorily, as in the benzo series.Both Z-(14a) and E-disulfides (15a) could be obtained from the Bunte salt and thiosulfonate by reaction with p-toluenethiol; the Z-disulfide readily isomerized to the E-isomer. 2,3-Dihydroxypropanethiol also could be converted to the Z and E disulfides (14b, 15b).Key words: Disulfides; dithiins; 1,4-dithiols; sulfur (extrusion of); trisulfides; trithiepins.
SULFINIC ACIDS AND RELATED COMPOUNDS. 16. SYNTHESES AND PROPERTIES OF SOME 4-(ALKYLDITHIO)- AND SUBSTITUTED 4-(ALKYLDITHIO)BUTANESULFINATE SALTS
Chandra, Ramesh,Field, Lamar
, p. 247 - 252 (2007/10/02)
Alkyl- and substituted alkyldithiobutanesulfinate salts of the structure RSS(CH2)4SO2Na were prepared in 62-81 percent yield by cleavage of 1,2-dithiane 1,1-dioxide (1) by thiolate salts.Compounds are reported with R=(CH3)3C (2), CH3(CH2)3 (3), CH3CH2 (4), HO(CH3)2 (5), HO2CCH2CH(CO2H) (6), NaO2S(CH2)4SS(CH2)3 (7), and NaO2S(CH2)4SS(CH2)5 (8).These compounds disproportionated in water to permit extraction of the symmetrical disulfide RSSR (3,5), or a mixture of RSSR and the dioxide 1 (2,4), or 1 only (6), or 1 plus insoluble polymer (7,8).The order of increasing resistance to disproportionation, where polymer was not involved, was estimated to be 3 6 ca. 4 /- 5 2.
